Use of alkoxylation products of epoxidized fats as antifoaming agents

Abstract

A method of controlling or preventing foam in an aqueous system is provided, wherein an effective amount of an alkoxylated, epoxidized fatty compound that has been ring-opened with a nucleophile is determined and added to the system. After ring opening with the nucleophile, the epoxidized fatty compound is alkoxylated with an alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide, and butylene oxide.

We claim: 
     
       1. A method of controlling or preventing foam in an aqueous system comprising the steps of determining an amount effective to control or prevent foam in the system of a compound prepared by alkoxylating an epoxidized fatty compound that has been ring-opened with a nucleophile with an alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide, and butylene oxide, and adding to the system the determined effective amount of the compound. 
     
     
       2. A method according to claim 1, wherein the alkoxylation is carried out in the presence of a catalyst. 
     
     
       3. A method according to claim 2, wherein the catalyst is selected from the group consisting of potassium hydroxide and sodium methylate. 
     
     
       4. A method according to claim 1, wherein the alkoxylation is carried out at a temperature of 110° C. to 200° C. and a pressure of 10 5  to 2×10 6  Pa, and the amount of alkylene oxide is 2% to 200% by weight, based on the weight of non-alkoxylated epoxidized fatty compound. 
     
     
       5. A method according to claim 4, wherein the alkoxylation is carried out at a temperature of 145° C. to 175° C. and a pressure of 3×10 5  to 5×10 5  Pa, and the amount of alkylene oxide is 20% to 100% by weight, based on the weight of non-alkoxylated epoxidized fatty compound. 
     
     
       6. A method according to claim 5 wherein the amount of alkylene oxide is 40% to 80% by weight, based on the weight of non-alkoxylated epoxidized fatty compound. 
     
     
       7. A method according to claim 1, wherein the epoxidized fatty compound is an epoxidized triglyceride, the nucleophile is a mixture of fatty acids, each of said acids containing 6 to 12 carbon atoms, and the amount of alkylene oxide is 40% to 80% by weight, based on the weight of non-alkoxylated epoxidized fatty compound. 
     
     
       8. A method according to claim 1, wherein the epoxidized fatty compound is selected from the group consisting of epoxidized triglycerides, epoxidized fatty acid esters of monohydric alcohols, epoxidized fatty alcohols, and epoxidized fatty alcohol esters. 
     
     
       9. A method according to claim 8, wherein the epoxidized fatty compound has 8 to 22 carbon atoms and 1 to 5 epoxide rings. 
     
     
       10. A method according to claim 8, wherein the epoxidized fatty compound is an epoxidized fatty alcohol ester of a monobasic carboxylic acid. 
     
     
       11. A method according to claim 8, wherein the epoxidized fatty compound is an epoxidized triglyceride derived by epoxidation of a fatty acid from a fat selected from the group consisting of beef tallow, palm oil, peanut oil, rapeseed oil, coriander oil, olive oil, fish oil, cottonseed oil, soybean oil, sunflower oil, and linseed oil. 
     
     
       12. A method according to claim 11, wherein the fat is selected from the group consisting of soybean oil and linseed oil. 
     
     
       13. A method according to claim 8, wherein the epoxidized fatty compound is an epoxidized fatty acid esters of a monohydric alcohol, said alcohol having 1 to 4 carbon atoms. 
     
     
       14. A method according to claim 13, wherein the epoxidized fatty compound is an epoxide of a compound selected from the group consisting of palmitoleic acid methyl ester, oleic acid methyl ester, elaidic acid methyl ester, petroselic acid methyl ester, linoleic acid methyl ester, erucic acid methyl ester, oleic acid butyl ester, and oleic acid i-butyl ester. 
     
     
       15. A method according to claim 8, wherein the epoxidized fatty compound is selected from the group consisting of epoxidized fatty alcohols and epoxidized fatty alcohol esters, said compound having 12 to 22 carbon atoms. 
     
     
       16. A method according to claim 15, wherein the epoxidized fatty compound is an epoxidized fatty alcohol ester of a monobasic carboxylic acid. 
     
     
       17. A method according to claim 16, wherein the epoxidized fatty compound is an epoxide of a compound selected from the group consisting of acetic acid oleyl ester, oleic acid oleyl ester, and erucic acid oleyl ester. 
     
     
       18. A method according to claim 1, wherein the nucleophile is a hydroxyfunctional compound selected from the group consisting of water, monohydric alcohols, polyhydric alcohols, and carboxylic acids. 
     
     
       19. A method according to claim 18, wherein the nucleophile is a monohydric alcohol containing 1 to 54 carbon atoms. 
     
     
       20. A method according to claim 19, wherein the nucleophile is selected from the group consisting of methanol, ethanol, 1-propanol, 2-propanol, n-butanol, pentanol, hexanol, 2-ethyl hexanol, cyclohexanol, benzyl alcohol, octanol, decanol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, erucyl alcohol, dimer diols derived by hydrogenation of dimer fatty acid esters, and trimer diols derived by hydrogenation of trimer fatty acid esters. 
     
     
       21. A method according to claim 19, wherein the nucleophile is a fatty alcohol containing 6 to 22 carbon atoms. 
     
     
       22. A method according to claim 18, wherein the nucleophile is a polyhydric alcohol containing 2 to 8 hydroxyl groups. 
     
     
       23. A method according to claim 18, wherein the nucleophile is a polyhydric alcohol selected from the group consisting of ethylene glycol, diethylene glycol, polyethylene glycols of molecular weight 300 to 1500, propane-1,2-diol, propane-1,3-diol, butane-1,4-diol, hexane-1,6-diol, neopentyl glycol, glycerol, trimethylol ethane, oligoglycerols having an average degree of condensation from 2 to 10, trimethylol propane, pentaerythritol, sorbitol, and sorbitan. 
     
     
       24. A method according to claim 23, wherein the nucleophile is selected from the group consisting of ethylene glycol, propane-1,2-diol, and trimethylol propane. 
     
     
       25. A method according to claim 18, wherein the nucleophile is a carboxylic acid containing 1 to 54 carbon atoms. 
     
     
       26. A method according to claim 25, wherein the carboxylic acid is selected from the group consisting of formic acid, acetic acid, propionic acid, fatty acids containing 6 to 22 carbon atoms, dimer fatty acid, trimer fatty acid, ricinoleic acid, hydroxystearic acid, and benzoic acid. 
     
     
       27. A method according to claim 18, wherein the nucleophile is a mixture of fatty acids, each of said acids containing 6 to 18 carbon atoms. 
     
     
       28. A method according to claim 27, wherein the fatty acids contain 6 to 12 carbon atoms. 
     
     
       29. A method according to claim 1, wherein the epoxidized fatty compound is an epoxidized triglyceride or a fatty acid ester of a monohydric alcohol, and the nucleophile is water. 
     
     
       30. A method according to claim 1, wherein the epoxidized fatty compound is an epoxidized triglyceride, and the nucleophile is a monohydric alcohol. 
     
     
       31. A method according to claim 30, wherein the monohydric alcohol is selected from the group consisting of methanol and fatty alcohols containing 8 to 18 carbon atoms. 
     
     
       32. A method according to claim 1, wherein the epoxidized fatty compound is an epoxidized triglyceride, and the nucleophile is a carboxylic acid. 
     
     
       33. A method according to claim 32, wherein the carboxylic acid is a mixture of carboxylic acids, said acids each containing 6 to 18 carbon atoms. 
     
     
       34. A method according to claim 33, wherein said carboxylic acids each contain 6 to 12 carbon atoms. 
     
     
       35. A method according to claim 33, wherein the mixture of carboxylic acids is a mixture of ricinoleic acid and hydroxystearic acid. 
     
     
       36. A method according to claim 1, wherein the epoxidized fatty compound is an epoxidized fatty acid ester and the nucleophile is a polyhydric alcohol. 
     
     
       37. A method according to claim 36, wherein the molar ratio of epoxidized fatty acid ester to polyhydric alcohol is 1:0.5 to 1:10. 
     
     
       38. A method according to claim 1, wherein the epoxidized fatty compound is an epoxidized fatty acid ester, and the nucleophile is a carboxylic acid. 
     
     
       39. A method according to claim 38, wherein the carboxylic acid is a mixture of carboxylic acids, said acids each containing 6 to 18 carbon atoms. 
     
     
       40. A method according to claim 39, wherein said carboxylic acids each contain 6 to 12 carbon atoms. 
     
     
       41. A method according to claim 39, wherein the mixture of carboxylic acids is a mixture of ricinoleic acid and hydroxystearic acid. 
     
     
       42. A method according to claim 1, wherein the molar ratio of epoxidized fatty compound to nucleophile is 1:10 to 10:1. 
     
     
       43. A method according to claim 42, wherein the ratio is 1:3 to 3:1. 
     
     
       44. A method according to claim 1, wherein the epoxidized fatty compound and the nucleophile are reacted at a temperature of 50° C. to 250° C. and a pressure of 10 5  to 10 6  Pa for a period of 1 to 6 hours. 
     
     
       45. A method according to claim 44, wherein the reaction is carried out in the presence of a catalyst. 
     
     
       46. A method according to claim 45, wherein the catalyst is selected from the group consisting of sulfuric acid and p-toluene sulfonic acid. 
     
     
       47. A method of controlling or preventing foam in an aqueous system comprising the steps of: (a) determining an amount effective to control or prevent foam in the system of a compound prepared by: i. reacting an epoxidized fatty compound selected from the group consisting of epoxidized triglycerides, epoxidized fatty acid esters of monohydric alcohols, epoxidized fatty alcohols, and epoxidized fatty alcohol esters with a nucleophile selected from the group consisting of water, monohydric alcohols, polyhydric alcohols, and carboxylic acids to effect at least partial opening of the epoxide rings of the epoxidized fatty compound; and   ii. alkoxylating the at least partially ring-opened epoxidized fatty compound with an alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide, and butylene oxide; and     (b) adding to the aqueous system the determined effective amount of the compound.